Diethylene Glycol Monoethyl Ether → Benzyl rac-alpha-[[[1-[[2-(2-ethoxyethoxy)ethoxy]carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate

HRID 275606Notes

Reaction equation

HRID 275606 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][OH:37])[CH3:30]>N1C=CC=CC=1>[CH2:29]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][C:17]([C:16]([S:13]([CH2:12][CH:11]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])(=[O:14])=[O:15])([CH3:21])[CH3:20])=[O:18])[CH3:30]

Participants

4

Reactant 2

HCID 8146Diethylene Glycol Monoethyl EtherHCID 20088482(RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

Product 1

HCID 54520543Benzyl rac-alpha-[[[1-[[2-(2-ethoxyethoxy)ethoxy]carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In an analogous manner to that of Example 2, paragraph (c), by reacting (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride and diethylene glycol monoethyl ether in pyridine there was obtained benzyl rac-α-[[[1-[[2-(2-ethoxyethoxy)ethoxy]carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate as a colourless oil, MS: 385 (M-COObenzyl)+.

Sources & evidence

ORD record
ord-51d0dce3f47d4a25bb4eaa964b16f1d1
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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